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Cheap flights from Chicago Midway Airport to San José from $178

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 6/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 9:46 pm
SJO
-
MDW
7h 21m
1 stop
$438Delta
Tue, Sep 22 - Wed, Sep 23
Delta Logo
5:59 pm - 11:58 am
MDW
-
SJO
18h 59m
2 stops
Delta Logo
1:23 pm - 9:45 pm
SJO
-
MDW
7h 22m
1 stop
$443Delta
Mon, Oct 5 - Thu, Oct 15
Delta Logo
6:00 am - 11:56 am
MDW
-
SJO
6h 56m
1 stop
Delta Logo
1:21 pm - 8:42 am
SJO
-
MDW
18h 21m
2 stops
$445Delta
Fri, Aug 14 - Wed, Aug 19
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
Southwest Logo
9:00 am - 5:40 pm
SJO
-
MDW
7h 40m
1 stop
$476Southwest
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
9:20 am - 6:40 pm
MDW
-
SJO
10h 20m
2 stops
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
$480Southwest
Mon, Sep 21 - Fri, Sep 25
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$484Southwest
Mon, Aug 24 - Wed, Sep 23
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
Southwest Logo
9:00 am - 9:50 pm
SJO
-
MDW
11h 50m
2 stops
$488Southwest
Mon, Aug 24 - Wed, Sep 23
Southwest Logo
1:10 pm - 7:00 pm
MDW
-
SJO
6h 50m
1 stop
Southwest Logo
9:00 am - 8:15 pm
SJO
-
MDW
10h 15m
2 stops
$492Southwest
Sun, May 24 - Thu, May 28
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 9:46 pm
SJO
-
MDW
7h 21m
1 stop
$493Delta
Sat, Sep 19 - Thu, Sep 24
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 8:42 am
SJO
-
MDW
18h 17m
2 stops
$498Delta
Mon, Sep 21 - Wed, Sep 23

Frontier flights from Chicago Midway Airport to San José

Our best Frontier deals on Chicago Midway Airport to San José flight tickets
Frontier
Aug 14
MDW3:22 pmChicago Midway
17h 58m
2 stops
SJO8:20 amSan José Juan Santamaria Intl
Aug 20
SJO9:35 amSan José Juan Santamaria Intl
11h 36m
2 stops
MDW10:11 pmChicago Midway
$529
Frontier
Jul 3
MDW4:10 pmChicago Midway
17h 10m
2 stops
SJO8:20 amSan José Juan Santamaria Intl
Jul 11
SJO9:35 amSan José Juan Santamaria Intl
11h 33m
2 stops
MDW10:08 pmChicago Midway
$592

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Sep 22
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
Sep 29
SJO1:25 pmSan José Juan Santamaria Intl
7h 21m
1 stop
MDW9:46 pmChicago Midway
$438
Delta
Oct 5
MDW5:59 pmChicago Midway
18h 59m
2 stops
SJO11:58 amSan José Juan Santamaria Intl
Oct 14
SJO1:23 pmSan José Juan Santamaria Intl
7h 22m
1 stop
MDW9:45 pmChicago Midway
$443
Delta
Aug 14
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
Aug 19
SJO1:21 pmSan José Juan Santamaria Intl
18h 21m
2 stops
MDW8:42 amChicago Midway
$445

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 3, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/22

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Wed 9/23

1:25 pm-9:46 pm

1 stop7h 21m

$438

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 10/5

5:59 pm-11:58 am

2 stops18h 59m

San José Juan Santamaria Intl

Thu 10/15

1:23 pm-9:45 pm

1 stop7h 22m

$443

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 8/14

6:00 am-11:56 am

1 stop6h 56m

San José Juan Santamaria Intl

Wed 8/19

1:21 pm-8:42 am

2 stops18h 21m

$445

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/22

10:10 am-6:40 pm

2 stops9h 30m

San José Juan Santamaria Intl

Tue 9/29

9:00 am-5:40 pm

1 stop7h 40m

$476

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/21

9:20 am-6:40 pm

2 stops10h 20m

San José Juan Santamaria Intl

Fri 9/25

9:00 am-9:30 pm

1 stop11h 30m

$480

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 8/24

10:05 am-6:40 pm

2 stops9h 35m

San José Juan Santamaria Intl

Wed 9/23

1:40 pm-11:10 pm

1 stop8h 30m

$484

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 8/24

10:05 am-6:40 pm

2 stops9h 35m

San José Juan Santamaria Intl

Wed 9/23

9:00 am-9:50 pm

2 stops11h 50m

$488

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 5/24

1:10 pm-7:00 pm

1 stop6h 50m

San José Juan Santamaria Intl

Thu 5/28

9:00 am-8:15 pm

2 stops10h 15m

$492

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 9/19

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Thu 9/24

1:25 pm-9:46 pm

1 stop7h 21m

$493

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/21

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Wed 9/23

1:25 pm-8:42 am

2 stops18h 17m

$498

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $512. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $690. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $514. Flights at noon are often more expensive with an average ticket price of $664.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Fastest flight time

6h 51m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José takes 6h 51m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San José

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 51m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,310 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Santa Elena
Dominical
San Gerardo de Dota
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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